Nitrogen → HCID 70386788, compound

HRID 1583494Notes

Reaction equation

HRID 1583494 reaction equation
C[O-].[Na+].C([O:6][CH2:7][CH3:8])=O.N#N.[CH2:11]([C:21]1[CH:30]=C2[C:24]([CH2:25][CH2:26][CH2:27][C:28]2=[O:31])=[CH:23][CH:22]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>C1(C)C=CC=CC=1>[OH:31][CH:28]=[C:27]1[CH2:26][CH2:25][C:24]2[C:8](=[CH:30][C:21]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:22][CH:23]=2)[C:7]1=[O:6]

Participants

6

Reactant 4

HCID 947NitrogenHCID 8025Ethyl formateHCID 10942334Sodium MethoxideHCID 135480317-Decyl-3,4-dihydronaphthalen-1(2H)-one

Product 1

HCID 70386788HCID 70386788, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of sodium methoxide (5.4 g, 40.5 mmoles), ethyl formate 7.4 g, 100 mmoles) and 100 mL dry toluene was cooled in an ice bath under inert atmosphere (N2 or Argon). A solution of 7-n-decyl-1-tetralone (11.5 g, 40 mmoles) in 100 mL dry toluene was added with rapid stirring. The ice bath was removed and the reaction was stirred at RT for 4 hours. The reaction was treated with 100 mL water and 100 l mL 6N HCl. The organic layer was separated and washed twice with 50 mL saturated NaCl, dried over anhydrous Na2SO4, filtered and evaporated to remove all the toluene. The oily residue was used for the next reaction without further purification.

Workup

  1. customThe ice bath was removed
  2. additionThe reaction was treated with 100 mL water and 100 l mL 6N HCl
  3. customThe organic layer was separated
  4. washwashed twice with 50 mL saturated NaCl
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customto remove all the toluene
  9. customThe oily residue was used for the next reaction without further purification

Sources & evidence

ORD record
ord-e78b483cb4914f8b9eee9126dda93f07
Source dataset
uspto-grants-1985_11
Patent number
US04552697

Reaction notes

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